JP2019523810A5 - - Google Patents
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- JP2019523810A5 JP2019523810A5 JP2019514163A JP2019514163A JP2019523810A5 JP 2019523810 A5 JP2019523810 A5 JP 2019523810A5 JP 2019514163 A JP2019514163 A JP 2019514163A JP 2019514163 A JP2019514163 A JP 2019514163A JP 2019523810 A5 JP2019523810 A5 JP 2019523810A5
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- -1 amine salt compound Chemical class 0.000 claims description 21
- 150000003141 primary amines Chemical class 0.000 claims description 7
- 150000001412 amines Chemical class 0.000 claims description 5
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 claims description 5
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 4
- 125000004432 carbon atoms Chemical group C* 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 21
- 125000003277 amino group Chemical group 0.000 claims 19
- 229910052736 halogen Inorganic materials 0.000 claims 18
- 239000004088 foaming agent Substances 0.000 claims 16
- 239000004604 Blowing Agent Substances 0.000 claims 12
- 229920005830 Polyurethane Foam Polymers 0.000 claims 11
- 239000000203 mixture Substances 0.000 claims 11
- 239000011496 polyurethane foam Substances 0.000 claims 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 11
- 150000002367 halogens Chemical class 0.000 claims 10
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims 9
- 125000005843 halogen group Chemical group 0.000 claims 9
- 125000001931 aliphatic group Chemical group 0.000 claims 5
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 5
- 150000001875 compounds Chemical class 0.000 claims 4
- 239000002994 raw material Substances 0.000 claims 4
- 239000011780 sodium chloride Substances 0.000 claims 4
- 125000006416 CBr Chemical group BrC* 0.000 claims 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 229920000642 polymer Polymers 0.000 claims 3
- 229920005862 polyol Polymers 0.000 claims 3
- 150000003077 polyols Chemical class 0.000 claims 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate dianion Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 2
- 150000001450 anions Chemical class 0.000 claims 2
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims 2
- 125000003118 aryl group Chemical group 0.000 claims 2
- 239000003054 catalyst Substances 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 239000000463 material Substances 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- AWMVMTVKBNGEAK-UHFFFAOYSA-N styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 claims 2
- 125000003944 tolyl group Chemical group 0.000 claims 2
- 239000004593 Epoxy Substances 0.000 claims 1
- 229920001730 Moisture cure polyurethane Polymers 0.000 claims 1
- 229920001228 Polyisocyanate Polymers 0.000 claims 1
- 125000002723 alicyclic group Chemical group 0.000 claims 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N ammonium hydroxide Chemical group [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims 1
- 125000005997 bromomethyl group Chemical group 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 150000001768 cations Chemical class 0.000 claims 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- GKIPXFAANLTWBM-UHFFFAOYSA-N epibromohydrin Chemical compound BrCC1CO1 GKIPXFAANLTWBM-UHFFFAOYSA-N 0.000 claims 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims 1
- 150000002118 epoxides Chemical class 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N oxane Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims 1
- 229920001281 polyalkylene Polymers 0.000 claims 1
- 229920000768 polyamine Polymers 0.000 claims 1
- 239000005056 polyisocyanate Substances 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims 1
- 150000003512 tertiary amines Chemical group 0.000 claims 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 1
- 125000001302 tertiary amino group Chemical group 0.000 description 4
- QUSNBJAOOMFDIB-UHFFFAOYSA-N ethyl amine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
Description
本願において、−+NR3R4H基は、−NR3R4+H基を指し、−+NR3H−基は、−NR3(+H)−基を指す。一般的に、有機アミンBは≧m個(例えば、m〜m+3個)の第一級アミン、第二級アミン及び/又は第三級アミン基を有し、オプションとして第四級アンモニウム基を有する。例を挙げると、CH3CH2 +NH2H(即ち、エチルアミンカチオン、CH3CH2NH2 +H)は、エチルアミンと一個の+Hイオンが結合されて形成されたものであって、ここで、B1+=CH3CH2 +NH2H又はCH3CH2 NH2 +Hであり、m=1、B=エチルアミンである。上記の式において、第一級アミン、第二級アミン及び/又は第三級アミン基は、−NR3R4基及び−NR3−基から選択される。 In the present application, - + NR 3 R 4 H group refers to a -NR 3 R 4+ H group, - + NR 3 H- group, -NR 3 (+ H) - refers to the group. Generally, the organic amine B has ≧m (eg, m to m+3) primary amine, secondary amine and/or tertiary amine groups, and optionally quaternary ammonium groups. .. For example, CH 3 CH 2 + NH 2 H (that is, ethylamine cation, CH 3 CH 2 NH 2 + H) is formed by combining ethylamine and one + H ion, , B 1+ =CH 3 CH 2 + NH 2 H or CH 3 CH 2 NH 2 + H, m=1, and B=ethylamine. In the above formula, primary amine, secondary amine and / or tertiary amine groups, -NR 3 R 4 group and -NR 3 - is selected from the group.
有機アミン類化合物Bは、m〜m+3個の第一級アミン、第二級アミン及び/又は第三級アミン基を有し、オプションとして第四級アンモニウム基の有機アミン類を有する。好ましくは、有機アミン類化合物Bは、2−200個の炭素原子(3−50個が好ましく、3−20個が更に好ましく、3−12個がより更に好ましい)の有機アミン化合物を有する。一般的に、それは上述のR基を有する。 The organic amine compound B has m to m+3 primary amine, secondary amine and/or tertiary amine groups, and optionally quaternary ammonium group organic amines. Preferably, the organic amine compound B has an organic amine compound of 2 to 200 carbon atoms (3 to 50 is preferable, 3 to 20 is more preferable, 3 to 12 is even more preferable). Generally, it has the R groups described above.
本願において、有機アミン類化合物B、又は≧m個(例えば、m〜m+3個)の第一級アミン、第二級アミン及び/又は第三級アミン基を有し且つオプションとして第四級アンモニウム基を有する有機アミン類化合物Bと、m個の+Hイオンが結合されてBm+になる。
In the present application, an organic amine compound B, or having ≧m (eg, m to m+3) primary amine, secondary amine and/or tertiary amine groups and optionally a quaternary ammonium group. The organic amine compound B having is bonded to m + H ions to form B m+ .
Claims (17)
An− [ Bm+ ]p (I)
式において、An−はCO2ドナーとしての−n価のアニオンであって、n=1又は2であり、
Bm+は、+1価のアンモニウムイオン、及び/又はm個の−+NR3R4H基及び/又は−+NR3H−基を有する一種類又は複数種類の有機アミンBのカチオンを含み、
m=1−5であり、
An−は、下記のアニオンから選択される一種類又は複数種類であり、
(a)炭酸イオン:CO3 2−;
(c)炭酸水素イオン:HO−COO−;
ここで、R3又はR4は、H、R、ヒドロキシル基又はアミノ基又はハロゲンで置換されていてもよいC1−C7脂肪族炭化水素基、ヒドロキシル基又はアミノ基又はハロゲンで置換されていてもよいC3−C7脂環式炭化水素基、又は、ヒドロキシル基又はアミノ基又はハロゲンで置換されていてもよいC6−C10芳香族炭化水素基からそれぞれ別々に選択され;
前提条件として、前記一般式(I)の化合物はNに結合されたR基を少なくとも一つ有し;
当該R基は、下記の基から選択される一種類又は複数種類であり、
(1a)H[OCH(R1a)CH(R2a)]q−;
(2a)H[OCH(R1a)CH(R2a)CH(R3a)]q−;又は、
(3a)H[OCH(R1a)CH(R2a)CH(R3a)CH(R4a)]q−;
ここで、qの値又は平均値は、q=1−3であり;R1a、R2a、R3a又はR4aは、H、ヒドロキシル基又はアミノ基又はハロゲンで置換されていてもよいC1−C7脂肪族炭化水素基、ヒドロキシル基又はアミノ基又はハロゲンで置換されていてもよいC3−C7脂環式炭化水素基、又は、ヒドロキシル基又はアミノ基又はハロゲンで置換されていてもよいC6−C10芳香族炭化水素基からそれぞれ別々に選択され;
ここで、有機アミン化合物(B)は、2−50個の炭素原子を有する有機アミン化合物であり;及び
発泡剤中の水の含有量は5−40wt%である、発泡剤。 A blowing agent comprising an organic amine salt compound having the following general formula (I) or a mixture of organic amine salt compounds having the following general formula (I):
A n− [B m+ ] p (I)
In the formula, A n− is a −n-valent anion as a CO 2 donor, and n=1 or 2,
B m+ includes a +1 valent ammonium ion, and/or a cation of one or more kinds of organic amine B having m − + NR 3 R 4 H groups and/or − + NR 3 H- groups,
m=1-5,
A n− is one kind or a plurality of kinds selected from the following anions,
(A) Carbonate ion: CO 3 2− ;
(C) bicarbonate ions: HO-COO -;
Here, R 3 or R 4 is substituted with H, R, a hydroxyl group, an amino group or a C 1 -C 7 aliphatic hydrocarbon group which may be substituted with a halogen, a hydroxyl group, an amino group or a halogen. which may be C 3 -C 7 cycloaliphatic hydrocarbon group, or, respectively independently selected from hydroxyl or amino group or C 6 -C 10 aromatic substituted with halogen hydrocarbon group;
As a prerequisite, the compound of general formula (I) has at least one R group attached to N;
The R group is one kind or plural kinds selected from the following groups,
(1a)H[OCH( R1a )CH( R2a )] q- ;
(2a)H[OCH( R1a )CH( R2a )CH( R3a )] q- ; or
(3a)H[OCH( R1a )CH( R2a )CH( R3a )CH( R4a )] q- ;
Here, the value or the average value of q is q=1-3; R 1a , R 2a , R 3a, or R 4a is C 1, which may be substituted with H, a hydroxyl group, an amino group, or a halogen. -C 7 aliphatic hydrocarbon group, a hydroxyl group or an amino group or a halogen substituted C 3 -C 7 cycloaliphatic hydrocarbon group or optionally substituted with a hydroxyl group or an amino group, or a halogen Each independently selected from a good C 6 -C 10 aromatic hydrocarbon group;
Here, the organic amine compound (B) is an organic amine compound having 2 to 50 carbon atoms; and the content of water in the foaming agent is 5 to 40% by weight.
発泡剤のpH値は7.8−9.5である、請求項3に記載の発泡剤。 The blowing agent according to claim 3, wherein the content of water in the blowing agent is 5-35 wt%, and/or the pH value of the blowing agent is 7.8-9.5.
発泡剤のpH値は8−9.5である、請求項4に記載の発泡剤。 The foaming agent according to claim 4, wherein the content of water in the foaming agent is 10-30 wt% 15-25 wt%, and/or the pH value of the foaming agent is 8-9.5.
一般式(I)の化合物は平均的に各分子が1.5−5個のR基を含有する、請求項1又は2に記載の発泡剤。 In the foaming agent, the total content of the compound of general formula (I) and water is 70-100%, based on the total weight of the foaming agent, and/or the compound of general formula (I) is on average Blowing agent according to claim 1 or 2, wherein the molecule contains 1.5-5 R groups.
前記有機アミン化合物(B)は、2−20個の炭素原子を有する有機アミン化合物である、請求項1又は2に記載の発泡剤。 Organic amine B has m to m + 3 one primary amine, secondary amine and / or tertiary amine group, or a quaternary ammonium group, and / or,
The foaming agent according to claim 1 or 2, wherein the organic amine compound (B) is an organic amine compound having 2 to 20 carbon atoms.
R基は、HOCH2CH2−、HOCH2CH(CH3)−、HOCH(CH3)CH2−、HOCH2CH(C6H5)−、HOCH(C6H5)CH2−、HOCH2CH(CH2Cl)−、HOCH(CH2Cl)CH2−、HOCH2CH(CBr3)−又はHOCH(CBr3)CH2−である、請求項1乃至4のいずれか1項に記載の発泡剤。 R 3 or R 4 may be substituted with H, R, a hydroxyl group or an amino group, or a C 1 -C 4 aliphatic hydrocarbon group which may be substituted with a halogen, a hydroxyl group, an amino group or a halogen. A cyclobutyl group or a cyclohexyl group, or a hydroxyl group, an amino group, or a phenyl group optionally substituted with halogen or a methylphenyl group, each of which is independently selected, and R 1a , R 2a , R 3a, or R 4a is H, methyl group, hydroxyl group, amino group or ethyl group optionally substituted with halogen, or hydroxyl group, amino group or propyl group optionally substituted with halogen or halogen group, hydroxyl group or amino group or halogen A cyclohexyl group which may be substituted with, or a hydroxyl group, an amino group, or a phenyl group which may be substituted with halogen, or a methylphenyl group, which are each independently selected,
R group, HOCH 2 CH 2 -, HOCH 2 CH (CH 3) -, HOCH (CH 3) CH 2 -, HOCH 2 CH (C 6 H 5) -, HOCH (C 6 H 5) CH 2 -, HOCH 2 CH (CH 2 Cl) -, HOCH (CH 2 Cl) CH 2 -, HOCH 2 CH (CBr 3) - or HOCH (CBr 3) CH 2 - in which any one of claims 1 to 4 The foaming agent described in 1.
当該方法は、第1の原料と第2の原料を水中で、触媒の存在下または非存在下で反応させることを含み、ここで、第1の原料は、下記から選択される一種類又は複数種類を含み:
R1R2N−COONH4、又はR1R2N−COOHの有機アミン類化合物(M)塩、ここで、R1又はR2は、H、ヒドロキシル基又はアミノ基又はハロゲンで置換されていてもよいC1−C7脂肪族炭化水素基、ヒドロキシル基又はアミノ基又はハロゲンで置換されていてもよいC3−C7脂環式炭化水素基、又は、ヒドロキシル基又はアミノ基又はハロゲンで置換されていてもよいC6−C10芳香族炭化水素基からそれぞれ別々に選択され、
(NH4)2CO3、又は炭酸有機アミン類化合物(M)塩、
HO−COONH4、又は有機アミン類化合物(M)の炭酸水素塩、
第2の原料は、下記から選択される一種類又は複数種類を含む:
前記の有機アミン類化合物(M)は、下記から選択される有機アミン類化合物である:
C1−C24ヒドロカルビルアミン類;
ジ(C1−C16ヒドロカルビル)アミン類;
C2−C14アルキレン基上にヒドロキシル基で置換されていてもよいC2−C14ヒドロカルビレン基ジアミン類;
C2−C14アルキレン基上にヒドロキシル基で置換されていてもよいC4−C16ポリアルキレンポリアミン類;
三個の第一級アミン基を有するC3−C18有機トリアミン類、又は四個の第一級アミン基を有するC5−C18有機テトラミン類;又は、
C2−C10アルコールアミン類
から選択され、発泡剤中の水の含有量は5−40wt%である、方法。 A method for producing a foaming agent, comprising:
The method includes reacting a first raw material and a second raw material in water in the presence or absence of a catalyst, where the first raw material is one or more selected from the following. Including type:
R 1 R 2 N-COONH 4 or an organic amine compound (M) salt of R 1 R 2 N-COOH, wherein R 1 or R 2 is substituted with H, a hydroxyl group or an amino group or halogen. Optionally a C 1 -C 7 aliphatic hydrocarbon group, a hydroxyl group or an amino group or a C 3 -C 7 alicyclic hydrocarbon group optionally substituted with a halogen, or a hydroxyl group, an amino group or a halogen Each independently selected from an optionally substituted C 6 -C 10 aromatic hydrocarbon group,
(NH 4 ) 2 CO 3 , or carbonate organic amine compound (M) salt,
HO-COONH 4 , or a hydrogen carbonate of an organic amine compound (M),
The second raw material comprises one or more selected from the following:
The organic amine compound (M) is an organic amine compound selected from the following:
C 1 -C 24 hydrocarbyl amines;
Di(C 1 -C 16 hydrocarbyl)amines;
C 2 -C 14 optionally substituted with a hydroxyl group on the alkylene radical C 2 -C 14 hydrocarbylene group diamines;
C 2 -C 14 optionally substituted with a hydroxyl group on the alkylene radical C 4 -C 16 polyalkylene polyamines;
C 3 -C 18 organic triamines having three primary amine groups, or a C 5 -C 18 organic tetramine compound having four primary amine groups; or
Is selected from C 2 -C 10 alcohol amines, content of water in the blowing agent is 5-40Wt%, method.
触媒はアンモニア水である、請求項11に記載の方法。 The epoxide is ethylene oxide, propylene oxide, epichlorohydrin, epibromohydrin, butylene oxide, or epoxy chlorobutane or styrene oxide, and a mixture of any two or more thereof, and/or
The method according to claim 11, wherein the catalyst is aqueous ammonia.
0.01−100重量%の請求項1乃至10のいずれか1項に規定の発泡剤、
0−50重量%の物理発泡剤、
0−5重量%の水、及び
0.0−99.99重量%のポリマーポリオール、を含み、
ここで、前記重量%は、ポリウレタン発泡組成物の総重量に基づくものである、ポリウレタン発泡組成物。 A polyurethane foam composition,
0.01-100% by weight of blowing agent as defined in any one of claims 1 to 10 ,
0 -50 wt% of the physical blowing agent,
0-5% by weight of water, and 0.0-99.99% by weight of polymer polyol,
Here, the said weight% is a polyurethane foam composition based on the total weight of a polyurethane foam composition.
0−40重量%の物理発泡剤、
0−4重量%の水、及び
20.0−99.9重量%のポリマーポリオール、を含み、
ここで、前記前記重量%は、ポリウレタン発泡組成物の総重量に基づくものである、請求項13に記載のポリウレタン発泡組成物。 0.1-80% by weight of blowing agent as defined in any one of claims 1 to 10 ,
0 -40 wt% of the physical blowing agent,
0-4 wt% water, and 20.0-99.9 wt% polymer polyol,
14. The polyurethane foam composition of claim 13 , wherein the weight percent is based on the total weight of the polyurethane foam composition.
0−40重量%の物理発泡剤、
0−4重量%の水、及び
40−97wt%のポリマーポリオール、を含み、
ここで、前記前記重量%は、ポリウレタン発泡組成物の総重量に基づくものである、請求項14に記載のポリウレタン発泡組成物。 3-60 wt% foaming agent as defined in any one of claims 1 to 10 ,
0 -40 wt% of the physical blowing agent,
0-4 wt% water, and 40-97 wt% polymer polyol,
15. The polyurethane foam composition of claim 14 , wherein the weight percent is based on the total weight of the polyurethane foam composition.
請求項13乃至15のいずれか1項に記載のポリウレタン発泡組成物がポリイソシアネート単体及び/又はイソシアネート末端のプレポリマーに混合され反応で形成されたものである、ポリウレタン泡沫材料。 A polyurethane foam material,
In which the polyurethane foam composition according to any one of claims 1 3 to 1 5 is formed by being mixed with a polyisocyanate alone and / or isocyanate-terminated prepolymers of the reaction, the polyurethane foam material.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201610393108.0 | 2016-06-02 | ||
CN201610393108.0A CN107089927B (en) | 2016-06-02 | 2016-06-02 | With as CO2The organic amine salt compounds of the anion of donor and its purposes as foaming agent |
PCT/CN2017/083948 WO2017206692A1 (en) | 2016-06-02 | 2017-05-11 | Organic amine salt compound having anions serving as co2 donors and application of same as foaming agent |
Publications (3)
Publication Number | Publication Date |
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JP2019523810A JP2019523810A (en) | 2019-08-29 |
JP2019523810A5 true JP2019523810A5 (en) | 2020-08-13 |
JP6800320B2 JP6800320B2 (en) | 2020-12-16 |
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JP2019514163A Active JP6800320B2 (en) | 2016-06-02 | 2017-05-11 | Organic amine salt compounds with anions as CO2 donors and their use as foaming agents |
Country Status (9)
Country | Link |
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US (1) | US20190152899A1 (en) |
EP (1) | EP3466924A4 (en) |
JP (1) | JP6800320B2 (en) |
KR (2) | KR20190004693A (en) |
CN (2) | CN107089927B (en) |
AU (1) | AU2017275049B2 (en) |
CA (1) | CA3025030C (en) |
RU (1) | RU2708457C1 (en) |
WO (1) | WO2017206692A1 (en) |
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CN109679130B (en) * | 2017-10-19 | 2021-09-07 | 山东理工大学 | Composite blowing agent comprising hexafluorobutene and organic alcohol amine salt compound |
CN109867767B (en) * | 2017-12-05 | 2021-08-10 | 补天新材料技术有限公司 | Polyurethane foaming method using carbon dioxide and organic amine in combination |
JP7327904B2 (en) * | 2018-03-30 | 2023-08-16 | マツダ株式会社 | Method for forming polyurethane foam using two-liquid reaction type urethane resin composition |
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